Morpholine → HCID 141573524, compound

HRID 1729562Notes

Reaction equation

HRID 1729562 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7]O)[CH2:3][CH2:2]1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:24]([NH:43][C:44]1[S:45][CH:46]=[C:47](/[C:49](=[N:81]/[O:82][CH3:83])/[C:50]([NH:52][CH:53]2[C:79](=[O:80])[N:55]3[C:56]([C:63]([O:65][CH:66]([C:73]4[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=4)[C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[S:64])=[C:57](C(=O)C)[CH2:58][S:59][C@H:54]23)=[O:51])[N:48]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N1CCOCC1.[F:90][C:91]([F:104])([F:103])[S:92]([O:95][CH2:96][CH:97]1[CH2:102][CH2:101][O:100][CH2:99][CH2:98]1)(=[O:94])=[O:93]>C(N(CC)CC)C.N1C=CC=CC=1>[F:103][C:91]([F:90])([F:104])[S:92]([O:95][CH2:96][CH:97]1[CH2:98][CH2:99][O:100][CH2:101][CH2:102]1)(=[O:93])=[O:94].[C:24]([NH:43][C:44]1[S:45][CH:46]=[C:47](/[C:49](=[N:81]/[O:82][CH3:83])/[C:50]([NH:52][CH:53]2[C:79](=[O:80])[N:55]3[C:56]([C:63]([O:65][CH:66]([C:73]4[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=4)[C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)=[S:64])=[C:57]([CH2:7][CH:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[CH2:58][S:59][C@H:54]23)=[O:51])[N:48]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

9

Reactant 5

HCID 8083MorpholineHCID 67749Trifluoromethanesulfonic anhydrideHCID 2773573(Oxan-4-yl)methanolHCID 19011570Tetrahydropyran-4-ylmethyl trifluoromethanesulfonateHCID 139642673HCID 139642673, compound

Product 2

HCID 19011570Tetrahydropyran-4-ylmethyl trifluoromethanesulfonateHCID 141573524HCID 141573524, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

Tetrahydropyran-4-ylmethyl trifluoromethanesulfonate was prepared in the same manner as in Example 27(a) from tetrahydropyran-4-yl-methanol (348 mg), pyridine (0.27 ml) and trifluoromethanesulfonic acid anhydride (931 mg). On the other hand, diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido]-3-acetylthio-3-cephem-4-carboxylate (866 mg) was reacted with morpholine and triethylamine in the same manner as in Example 27(b), followed by reacting the resulting reaction product with the tetrahydropyran-4-ylmethyl trifluoromethanesulfonate in the same manner as in Example 27(b). The reaction solution so obtained was post-treated in the same manner as in Example 27(b) and the produced compound was recovered and purified similarly to Example 27 (b) to afford the titled compound (904 mg; 98%).

Workup

  1. customThe reaction solution so obtained
  2. additionwas post-treated in the same manner as in Example 27(b)
  3. customthe produced compound was recovered

Sources & evidence

ORD record
ord-9f19f6da194e41b19e41081da01a2942
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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